^(13)C同位素标记DDT、DDD、DDE的简便合成  

Facile Synthesis of Isotopically ^(13)C-labeled p,p′-DDT,p,p′-DDD and p,p′-DDE

作　　者：王智楠 全海源 胡宇钊 王留洋 蒋志福[1] 梅向东[1] 宁君[1] 折冬梅[1] WANG Zhi-nan;QUAN Hai-yuan;HU Yu-zhao;WANG Liu-yang;JIANG Zhi-fu;MEI Xiang-dong;NING Jun;SHE Dong-mei(Institute of Plant Protection,Chinese Academy of Agricultural Sciences,Beijing 100193,China)

机构地区：[1]中国农业科学院植物保护研究所,北京100193

出　　处：《化学试剂》2021年第6期848-851,共4页Chemical Reagents

基　　金：国家重点研究发展计划项目(2016YFD0200201)。

摘　　要：有机氯农药滴滴涕(双对氯苯基三氯乙烷,DDT)作为一种持久性有机污染物,在环境中长时间滞留,并逐步代谢为更加稳定的滴滴伊(1,1-二氯-2,2-双(4-氯苯基)乙烯,DDE)和滴滴滴(双(6-羟基-2-萘)二硫,DDD)。同位素稀释质谱法(IDMS)是国际上唯一认可的痕量和超痕量检测的权威性检测方法。稳定同位素标记产品是该方法的物质基础。报道了^(13)C_(12)标记p,p′-DDT、p,p′-DDD和p,p′-DDE的合成。以^(13)C_(6)-苯为同位素标记原料,通过氧氯化得^(13)C_(6)-氯苯,^(13)C_(6)-氯苯分别与三氯乙醛水合物和二氯乙醛水合物经浓硫酸催化缩合制得^(13)C_(12)-DDT和^(13)C_(12)-DDD,以聚乙二醇-600为相转移催化剂,^(13)C_(12)-DDT脱氯化氢制得^(13)C_(12)-DDE。该方法产率高、产品纯度高、操作简便,可为同位素标记的二氯二苯基三氯乙烷类化合物(DDTs)的合成提供参考。As a persistent organic pollutant,the organochlorine pesticide dichlorodiphenyltrichloroethane(DDT)stays in the environment for a long time and is gradually metabolized into more stable 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene(DDE)and 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane(DDD).Isotope dilution mass spectrometry(IDMS)is the only authoritative detection method recognized internationally for testing trace and ultra-trace substances.Stable isotope-labeled standards are the material basis for this assay.The ^(13)C_(12)-labeled p,p′-DDD and p,p′-DDE were first reported in this paper.^(13)C_(6)-Chlorobenzene was produced via oxychlorination from ^(13)C_(6)-benzene,and subsequent sulphuric acid-catalyzed condensation with chloral hydrate and dichloroacetaldehyde hydrate yielded ^(13)C_(12)-p,p′-DDT and ^(13)C_(12)-p,p′-DDD,respectively.Then ^(13)C_(12)-p,p′-DDE was synthesized by catalytic dehydrochlorination method from ^(13)C_(12)-p,p′-DDT using polyethylene glycol 600 as phase transfer catalyst.This method has a higher yield,fewer by-products and an easier handling process,which provides a reference for the isotope-labeled synthesis of isotope-labeled dichlorodiphenyltrichloroethane compounds(DDTs).

关 键 词：^(13)C标记 ^(13)C_(6)-氯苯 二氯二苯基三氯乙烷类化合物 标记合成 

分 类 号：TQ421.6[化学工程]